Vacation. Simplified.

Tips for Traveling with Your Boss

July 13, 2018

Business travel can often be fraught with stress, especially so when accompanying your boss. If you are on a business trip with your boss you need to be your most efficient, competent self. Show her skills and expertise in ways she doesn’t typically get to see. We spoke to business travel expert Road Warriorette for suggestions on how to make the best impression on a business trip with a superior.

Plan, plan, and plan some more. Your goal for this trip is to be over-prepared before you ever leave. If there are any items that need to arrive in advance of your visit be sure to ship them with plenty of time, watch any tracking information, and confirm your items’ arrival. Also, it sounds obvious but know where you’re going upon landing. Make sure you have all the logistical information you need at your fingertips, including addresses for your office and hotel, car reservation information, and your schedule. Any travel-related information can be found in your UNIGLOBE app, and you can use scheduling apps to track everything else. Another tip: If you have trouble making conversation with superiors think about potential topics ahead of your trip.

Don’t check your bag unless your boss does. Typically my advice is to avoid checking your bag altogether, in order to save time, money, and potential inconvenience. However, if you know your boss will be checking then it should be fine if you check as well. If you plan to carry your bag make sure that it fits within airline guidelines and you are able to lift it easily into the overhead bins.

Don’t worry about sitting together on the plane. Most business travellers prefer not to sit by coworkers on flights, whether they’re superiors, colleagues, or direct reports. This is very normal. Also, it’s unlikely that tickets purchased separately would be seated together.

Look productive. If you do happen to be sitting together, if your boss is working you should look productive as well. If work isn’t an option try to avoid controversial book titles or magazines.

Dress appropriately during off-times. Unless you go to dinner straight from the office it’s unlikely you’ll be wearing suits to dinner. Make sure your off-time clothing is comfortable yet looks put together. Stay away from ripped jeans, workout clothes, or anything that looks too much like club-wear. Dark jeans or slacks with a nice shirt is typically a safe choice for most restaurants.

Avoid gossip. After a full day of meetings and a long dinner, it’s not uncommon to feel more comfortable speaking freely. Regardless, make sure your conversation remains professional in regards to colleagues and customers. Appearing to gossip about coworkers is not going to do you any favours.

Follow your boss’s lead. Don’t order a drink at dinner if your boss doesn’t, unless you’re certain it’s part of your company’s culture. If your boss doesn’t order dessert or coffee, follow suit. If you have a boss who likes to indulge don’t feel like you have to keep up. Instead, switch to club soda and lime or water. Be sure to watch your own alcohol intake as being intoxicated in front of your boss is certainly not the impression you want to make.

Overall, the goal is to appear highly competent and low maintenance. Planning, organization, and staying observant will ensure you make the best impression possible.